CN106833005A - A kind of method for preparing permeability azo organic pigment high - Google Patents
A kind of method for preparing permeability azo organic pigment high Download PDFInfo
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- CN106833005A CN106833005A CN201710058892.4A CN201710058892A CN106833005A CN 106833005 A CN106833005 A CN 106833005A CN 201710058892 A CN201710058892 A CN 201710058892A CN 106833005 A CN106833005 A CN 106833005A
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0014—Influencing the physical properties by treatment with a liquid, e.g. solvents
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- Chemical Kinetics & Catalysis (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
The present invention relates to a kind of method for preparing permeability azo organic pigment high, step A, aromatic primary amine are obtained diazol through diazotising, step B, the diazol are reacted with coupling component, synthesize pigment compound, step C, through pigmentation and surface modification treatment, pigment product is obtained, " impurity " compound of polar functionalities is introduced in pigment, using CONH2Stronger polarity, on the one hand with outside water molecules, prevents the increase of pigment particles, control pigment particle size distribution, for the pigment for obtaining the transparency provides safeguard；On the other hand, in pigmentation processing procedure, the intermolecular hydrogen bonding for forming multinode with pigment host compound is combined, and forms stable pigments crystal structure, improves heat-resisting, the resistance to migration energy of pigment；And CONH2Introducing, increased the anchoring group in pigment structure, it is easy to the introducing of surface conditioning agent, making the application performance of pigment is preferably improved.
Description
Technical field
In particular it is that one kind prepares the organic face of permeability azo high the present invention relates to fine chemistry industry preparing technical field
The method of material.
Background technology
Azo organic pigment refers to the organic pigment containing azo group (- N=N-) in chemical constitution, accounts for organic pigment total
More than the 60% of amount, is widely used in ink, coating, rubber, color paste of printing coating.To meet the need of different purposes
Ask, be developed the pigment of various characteristics, high transparency pigment is one kind therein, can be used for the fields such as printing-ink.
The factor of the influence organic pigment transparency is mainly particle size and size distribution.But in pigment application, particle diameter
Size and particle diameter distribution directly influence dispersiveness of the pigment in applicating medium, heat resistance, resistance to migration, form and aspect and tinting strength, tinting power
Deng application performance.Some pigment productions business often in order to meet the high transparency of product, the crystalline growth of reduction pigment intentionally, from
And make the application stability of product poor, influence quality.Therefore the transparency of change pigment is on the premise of stable application performance
Purport of the invention.
In Chinese invention patent specification CN1687252A, the microcapsules technology of, cladding broken using grinding is entered to pigment
Row surface is modified, and makes the modified surface of pigments in surface by polymer overmold, so as to avoid the reunion of granules of pigments, is had
The transparent pigment of good fluidity, easily dispersion and stability.
In Chinese invention patent specification CN1175053A, U.S. patent Nos specification US2006082690A, using micro-
Channel reactor, jet mixer device etc. complete diazo liquid, the hybrid reaction of coupling solution, prepare the organic pigment of azo, can
The particle diameter distribution of pigment, the transparency more usual scheme two-stage high of gained pigment, tinting strength, tinting power is effectively controlled also to significantly improve.
In Chinese invention patent specification CN1563202, common diazotising is carried out using the compound containing aminobenzenesulfonic acid, so
After be coupled.Gained pigment has improvement compared with single structure pigment application performance.
In Chinese invention patent specification CN1569968, protection adds female with pigment in benzimidazolone pigment crude product
Body structure proximate benzimidazolone derivatives, together carry out pigmentation and surface treatment, improve its dispersiveness and mobility, realize
The modified purpose of surface of pigments.
Chinese invention patent specification CN101962489 describes a kind of benzimidazolone pigment nano-scale particle for preparing
Method, the method provides one or more by benzimidazolone, pyridine derivate, alkylated benzenes by benzimidazolone pigment
And the steric bulk stabilizer of alkyl derivative and its mixture composition of imidazoquinolone compounds aromatic acid, formed with non-co-
Valence link mode is combined with steric bulk stabilizer, to limit the degree of grain growth and aggregation, and produces nano-sized pigments
Particle, there is provided meet the requirement of the specific use pigment such as piezoelectric ink jet printing, favorably ensures the reliability of ink jet printing and by face
Jet caused by material particle aggregation is blocked.
Chinese invention patent specification CN101962489 describes organic and inorganic composite pigment.This method is mainly logical
Cross absorption and deposition by organic pigment be coated on inorganic compound (such as aluminum oxide, aluminium hydroxide, silica, silica,
Titanium dioxide, kaolin and montmorillonite etc.) core on, so as to form new organic pigment particle.This processing method is combined
The superior heat resistance of inorganic pigment, fast light, weatherability, originally adding lustre to also in relation with organic pigment, it is high to compose complete, bright in colour, tinting strength, tinting power
The features such as.Its dispersion in water can also be improved by selecting inorganic core feature.By select inorganic core size distribution come
The size of pigment particles is controlled, the aggregation of organic pigment can be effectively prevented.This coated pigment can be used for plastics, rubber etc.
Coloring, and advertisement, bridge, road and signal paint etc..
The content of the invention
The technical problems to be solved by the invention are to provide a kind of method for preparing high transparency azo organic pigment, system
Standby high transparency azo organic pigment forms stable pigments crystal structure, improves heat-resisting, the resistance to migration energy of pigment.
In order to solve the above technical problems, the technical scheme that the present invention takes is：One kind prepares the organic face of permeability azo high
The method of material, comprises the following steps：
Step A, aromatic primary amine are obtained diazol through diazotising；
Step B, the diazol are reacted with coupling component, synthesize pigment compound；
Step C, through pigmentation and surface modification treatment, obtain pigment product；
In step, the aromatic primary amine carries out diazo-reaction and the diazonium is obtained with the compound (1) shown in formula 1
Salt, then carry out coupling reaction with the coupling component；
Or in stepb, the diazol with containing compound (2)-(4) shown in formula 2-4 in it is at least one
Coupling component carries out coupling reaction；
Wherein, R in formula1、R2、R3、R4Can be：H、CH3、CH2CH3、COOH、COOCH3、COOCH2CH3、OCH3、OCH2CH3、
Cl、CONH2；M, n are the integer of 0-20.
Improved as one kind of above-mentioned technical proposal, wherein：Compound (1) addition shown in the formula 1 is main body face
Expect the mol ratio 0-20% of compound.
Improved as one kind of above-mentioned technical proposal, wherein, compound (1) addition shown in the formula 1 is main body face
Expect the mol ratio 0.1-5% of compound.
Improved as one kind of above-mentioned technical proposal, wherein, compound (2) addition shown in the formula 2 is main body face
Expect the mol ratio 0-20% of compound.
Improved as one kind of above-mentioned technical proposal, wherein, compound (2) addition shown in the formula 2 is main body face
Expect the mol ratio 0.1-5% of compound.
Improved as one kind of above-mentioned technical proposal, wherein：Compound (3) addition shown in the formula 3 is main body face
Expect the mol ratio 0-20% of compound.
Improved as one kind of above-mentioned technical proposal, wherein：Compound (3) addition shown in the formula 3 is main body face
Expect the mol ratio 0.1-5% of compound.
Improved as one kind of above-mentioned technical proposal, wherein：Compound (4) addition shown in the formula 4 is main body face
Expect the mass ratio 0-20% of compound.
Improved as one kind of above-mentioned technical proposal, wherein：Compound (4) addition shown in the formula 4 is main body face
Expect the mass ratio 0.1-5% of compound.
Improved as one kind of above-mentioned technical proposal, wherein：In step C, the pigmentation water phase, organic solvent or
Carried out in mixed solvent, the temperature of pigmentation is at 50-200 DEG C.
The present invention compared with prior art, due in pigment introduce polar functionalities " impurity " compound, using-
CONH2Stronger polarity, on the one hand with outside water molecules, prevents the increase of pigment particles, and control pigment particle size is distributed,
For the pigment for obtaining the transparency provides safeguard；On the other hand, in pigmentation processing procedure, form many with pigment host compound
The intermolecular hydrogen bonding of node is combined, and forms stable pigments crystal structure, improves heat-resisting, the resistance to migration energy of pigment；And-CONH2
Introducing, increased the anchoring group in pigment structure, it is easy to the introducing of surface conditioning agent, the application performance of pigment is obtained more
Good improvement.
Specific embodiment
The following example is described in detail to present invention.
The present invention provides a kind of method for preparing high transparency azo organic pigment, prepares high transparency azo organic
Pigment forms stable pigments crystal structure, improves heat-resisting, the resistance to migration energy of pigment.The present invention is by pigment preparation process
Aromatic amine compound with-CONH2 bases is incorporated into pigment compound to realize.There is following four implementation method.
Mode one, with-CONH2Aromatic amine compound as diazo component, and pigment main body diazo component diazonium together
Change, be prepared into diazonium salt solution, coupling reaction is completed with coupling component, through pigmentation and modification, obtain pigment product.Should
The structure of aromatic amine compound is compound (1) as shown in Equation 1.
Wherein R1Can be：H、CH3、CH2CH3、COOH、COOCH3、COOCH2CH3、OCH3、OCH2CH3、Cl、CONH2。
Mode two, with-CONH2Aromatic amine compound as coupling component, together with pigment coupling component, with pigmentation
There is coupling reaction, synthetic dyestuff compound in the diazonium salt solution of compound, then through pigmentation and surface modification treatment, obtain pigment
Product.
To the light color azo dyes such as Huang, orange, add with-CONH2The structure of compound is compound as shown in Equation 2
(2)。
Wherein R2Can be：H、CH3、CH2CH3、COOH、COOCH3、COOCH2CH3、OCH3、OCH2CH3、Cl、CONH2。
To the dark color azo dyes such as red, brown, add with-CONH2The structure of compound is compound as shown in Equation 3
(3)。
Wherein R3Can be：H、CH3、CH2CH3、COOH、COOCH3、COOCH2CH3、OCH3、OCH2CH3、Cl、CONH2。
Mode three, with-CONH2Aromatic amine compound as reaction promoter participate in pigment preparation.Added with-
CONH2The structure of aromatic amine compound be the compound (4) shown in formula 4.
Wherein R4Can be：H、CH3、CH2CH3、COOH、COOCH3、COOCH2CH3、OCH3、OCH2CH3、Cl、CONH2；M, n are
0~20 integer.
Mode four, using two or more mode of any of the above.
Four kinds of implementation methods to more than, the mol ratio of required compound (1) addition and body pigment compound for 0~
20%, preferably 0.1%~5%；Compound (2) or (3) addition and the mol ratio of body pigment compound are 0~20%, excellent
Select 0.1~5%；Compound (4) addition is 0~20%, preferably 0~15% with the mass ratio of body pigment compound.
The preparation method of pigment of the invention required is adapted to the organic pigment of azo, including contains monoazo pigment, double
AZOpigments；Specific pigment structure type includes biphenyl class, acetanilide class, biacetyl acetanilide class, condensation azo, naphthalene
Phenol series, azo lake class and azo benzo imidazolone pigment.
In implementation method three, compound (4) can be diazo-reaction process, coupling reaction mistake in pigment adition process
Journey, or added when surface of pigments is processed, pay the utmost attention to be added in coupling reaction process with the aqueous solution or emulsion form.
, using the general method in this area, preferential recommendation is in aqueous medium for pigmentation and surface treatment in present invention implementation
Middle implementation, 50~150 degree for the treatment of temperature.
The present invention is had the special feature that：
Utilization-CONH of the present invention2Stronger polarity, on the one hand with outside water molecules, prevents the increasing of pigment particles
Greatly, control pigment particle size distribution, for the pigment for obtaining the transparency provides safeguard；On the other hand, in pigmentation processing procedure, with
Pigment host compound formed multinode intermolecular hydrogen bonding combine, formed stable pigments crystal structure, improve pigment it is heat-resisting,
Resistance to migration energy；And-CONH2Introducing, increased the anchoring group in pigment structure, it is easy to the introducing of surface conditioning agent, make
The application performance of pigment is preferably improved.
Additionally, the present invention is the improvement project of implementation under the existing preparation process condition of AZOpigments, technology of preparing change is small,
Effect is substantially, convenient to carry out and do not increase other production costs.
Embodiment 1：The preparation of pigment yellow 155
By 20.27 parts of 2- amino dimethyl terephthalate (DMT)s, 0.45 part of 3- amino -4- methyl benzamide and 39.9 parts
32% hydrochloric acid and 150 parts of water, are beaten together at room temperature.Form its hydrochloric acid saline suspension.It is on the rocks to cool to 0 DEG C, plus 23.46
The sodium nitrite solution of part 30%, carries out diazo-reaction, obtains transparent diazonium salt solution.
13.8 parts of biacetyl acetyl-p-phenylenediamines and 4.4 parts of NaOH, 100 parts of water stirrings, obtain clear solution.Add
0.2 part of emulsifier os -15 stirs with 0.1 part of dodecyl benzyl dimethyl ammonium chloride.9 parts of sodium acid carbonates are added, is obtained
Coupling solution；Wait to be coupled.
The 10% of taking-up diazonium salt solution gross weight adjusts pH to 3 in being put into reactor as bottom liquid, addition sodium acetate,
15 DEG C of temperature.Under stirring, by remaining diazonium salt solution and coupling solution with 2:1 mol ratio (waiting chemical reaction amount) is continuous slow
It is added in the liquid of bottom, until diazol is all added, about needs 2 hours.Remaining coupling solution is slowly added to, until H acid solutions are examined
Untill surveying there is no diazol excess, this is coupling terminal.Continue to stir 30min, be heated to 90 DEG C, be incubated 1 hour, cooling,
Filtering, washing, drying and crushing obtain pigment sample.
Embodiment 2：The preparation of pigment yellow 155
Difference from Example 1 is that the input amount of diazo component is 20.27 parts of 2- amino terephthalic acid (TPA) diformazans
Ester, 0.41 part of 4- aminobenzamide.
Embodiment 3：：The preparation of pigment yellow 155
Difference from Example 1 is that the input amount of diazo component is 20.27 parts of 2- amino terephthalic acid (TPA) diformazans
Ester, 0.58 part of 3- amino -4- methyl formate yl-benzamide.
Comparative example 1
It is that diazo component is with the difference of embodiment one as the method with amido compounds is added without
20.9 parts of 2- amino dimethyl terephthalate (DMT)s.
Embodiment 1-3 is compared with the gained pigment sample of comparative example 1, using pigment industries such as GB1708-79
Upper universal test method, compares pigment transparency, dispersiveness, tinctorial strength and coloured light, obtains following result.
| Project | Transparency | Dispersiveness | Tinting strength, tinting power | Coloured light |
| Comparative example 1 | Standard | Standard | 100 | Standard |
| Embodiment 1 | It is more saturating | Preferably | 108 | Approximately arrive micro- green |
| Embodiment 2 | It is more saturating | It is micro- good | 105 | Approximately arrive micro- red |
| Embodiment 3 | It is more saturating | It is micro- good | 110 | Approximately arrive micro- green |
Embodiment 4：The preparation of pigment Yellow 12
By 16.3 parts of 3.3`- dichlorobenzidine hydrochlorides, 150 parts of water, the 20 parts of mixed in hydrochloric acid of concentration 32% stirrings, drop on the rocks
To 0~5 DEG C, 30% aqueous solution for adding 24 parts of natrium nitrosums to be made into carries out diazo-reaction to temperature, prepares diazonium salt solution.
By 17.17 parts of AAAs, 0.66 part to formamido group AAA, 150 parts of water, 8 parts of hydroxides
Sodium mixes, stirring and dissolving.Adjustment temperature on the rocks is less than 5 DEG C, adds acetic acid, and it is 3~7 to adjust pH.
Diazonium salt solution is slowly added in 1.5h~2h carries out coupling reaction, after all adding, continues to stir 30min,
90 DEG C are heated to, the aqueous slkali of 3.3g rosin is added, 15min is stirred, calcium chloride is added, 30min is stirred, cooling filtering is dried
Obtain pigment sample.
Embodiment 5：The preparation of pigment Yellow 12
Difference from Example 4 is that 0.75g 3- methoxies are replaced with to formamido group AAA by 0.66 part
Base -4- formamido AAAs.
Embodiment 6：The preparation of pigment Yellow 12
Difference from Example 4 is to formamido group acetoacetyl benzene by 17.17 parts of AAAs, 0.66 part
Amine replaces with the condensation product of 17.7 AAAs, 3g p-benzoyls and oxirane.
Comparative example 2
It is by 17.17 parts of acetyl with example IV difference as the method with amido compounds is added without
Antifebrin, 0.66 part 17.7g AAAs are replaced with to formamido group AAA.
Embodiment 4-6 is compared with the gained pigment sample of comparative example 2, using pigment industries such as GB1708-79
Upper universal test method, compares pigment transparency, dispersiveness, tinctorial strength and coloured light, obtains following result.
| Project | Transparency | Dispersiveness | Tinting strength, tinting power | Coloured light |
| Comparative example 2 | Standard | Standard | 100 | Standard |
| Embodiment 4 | It is more saturating | It is micro- good | 109 | Approximately arrive micro- green |
| Embodiment 5 | It is more saturating | It is micro- good | 104 | Approximately arrive micro- red |
| Embodiment 6 | It is micro- | Preferably | 101 | Approximately |
Embodiment 7：The preparation of pigment red 146
By 11.74 parts of fast red KD bases, 0.23 part of 3- amino-4-methoxyl benzoyl, 17.11 part of 32% hydrochloric acid, 120 parts of water
Mixing, stirring is on the rocks to be cooled to less than 0 DEG C.11.85 parts of natrium nitrosums are configured to the aqueous solution of concentration 30%, are added to
State in material, diazo-reaction is carried out at 0~5 DEG C, obtain clear solution.
By 18.23g apthol AS-LCs, 150 parts of water and 15 part 40% of sodium hydroxide solution mix, and agitating heating makes fully
Dissolving.Filtering, removes insoluble matter, adds water and adjusts to 400 parts.
1 part of acetic acid is added in diazonium salt solution, is stirred.In stirring, charging rate is controlled, add coupling component molten
Liquid, by temperature controlled water baths in 12~15 DEG C, used time 1h；Circle testing inspection is oozed by H acid, it is ensured that gained slurry just not point
It is red.
It is heated to 90 DEG C and is incubated 1 hour, cooling filtering washing, dry pigment sample.
Embodiment 8：The preparation of pigment red 146
Difference from Example 7 be by 0.23 part of 3- amino-4-methoxyl benzoyl replace with 0.26 part of 3- amino-
4- chlorobenzamides.
Embodiment 9：The preparation of pigment red 146
12.1 parts of fast red KD bases, 17.11 part of 32% hydrochloric acid, 120 parts of water are mixed, stirring is on the rocks to be cooled to less than 0 DEG C.
11.85 parts of natrium nitrosums are configured to the aqueous solution of concentration 30%, are added in above-mentioned material, it is anti-to carry out diazotising at 0~5 DEG C
Should, obtain clear solution.
By 18.23g apthol AS-LCs, 150 parts of water and 15 part 40% of sodium hydroxide solution mix, and agitating heating makes fully
Dissolving.Filtering, removes insoluble matter, adds water and adjusts to 400 parts.
1 part of condensation product of acetic acid, 2.5 parts of p-benzoyls and oxirane is added in diazonium salt solution, stirring is equal
It is even.In stirring, charging rate is controlled, coupling component solution is added, by temperature controlled water baths in 12~15 DEG C, 1 hour used time；
Circle testing inspection is oozed by H acid, it is ensured that gained slurry is not just put red.
It is heated to 90 DEG C and is incubated 1 hour, cooling filtering, dry pigment sample.
Comparison example 3
As the method with amido compounds is added without, it is a difference in that 11.74 parts of red bases with embodiment seven
KD, 0.23 part of 3- amino-4-methoxyl benzoyl replace with 12.1 parts of fast red KD bases.
Embodiment 7-9 is compared with the gained pigment sample of comparative example 3, using pigment industries such as GB1708-79
Upper universal test method, compares pigment transparency, dispersiveness, tinctorial strength and coloured light, obtains following result.
Claims (10)
1. a kind of method for preparing permeability azo organic pigment high, comprises the following steps：
Step A, aromatic primary amine are obtained diazol through diazotising；
Step B, the diazol are reacted with coupling component, synthesize pigment compound；
Step C, through pigmentation and surface modification treatment, obtain pigment product；It is characterized in that：
In step, the aromatic primary amine carries out diazo-reaction and the diazol is obtained with the compound (1) shown in formula 1, then
Coupling reaction is carried out with the coupling component；
Or in stepb, the diazol with contain at least one coupling in compound (2)-(4) shown in formula 2-4
Component carries out coupling reaction；
Wherein, R in formula1、R2、R3、R4Can be：H、CH3、CH2CH3、COOH、COOCH3、COOCH2CH3、OCH3、OCH2CH3、Cl、
CONH2；M, n are the integer of 0-20.
2. a kind of method for preparing permeability azo organic pigment high according to claim 1, it is characterised in that：The formula
Compound (1) addition shown in 1 is the mol ratio 0-20% of main body pigment compound.
3. a kind of method for preparing permeability azo organic pigment high according to claim 1, it is characterised in that：The formula
Compound (1) addition shown in 1 is the mol ratio 0.1-5% of main body pigment compound.
4. a kind of method for preparing permeability azo organic pigment high according to claim 1, it is characterised in that：The formula
Compound (2) addition shown in 2 is the mol ratio 0-20% of main body pigment compound.
5. a kind of method for preparing permeability azo organic pigment high according to claim 1, it is characterised in that：The formula
Compound (2) addition shown in 2 is the mol ratio 0.1-5% of main body pigment compound.
6. a kind of method for preparing permeability azo organic pigment high according to claim 1, it is characterised in that：The formula
Compound (3) addition shown in 3 is the mol ratio 0-20% of main body pigment compound.
7. a kind of method for preparing permeability azo organic pigment high according to claim 1, it is characterised in that：The formula
Compound (3) addition shown in 3 is the mol ratio 0.1-5% of main body pigment compound.
8. a kind of method for preparing permeability azo organic pigment high according to claim 1, it is characterised in that：The formula
Compound (4) addition shown in 4 is the mass ratio 0-20% of main body pigment compound.
9. a kind of method for preparing permeability azo organic pigment high according to claim 1, it is characterised in that：The formula
Compound (4) addition shown in 4 is the mass ratio 0.1-5% of main body pigment compound.
10. a kind of method for preparing permeability azo organic pigment high according to any one of claim 1 to 9, it is special
Levy and be：In step C, the pigmentation is carried out in water phase, organic solvent or mixed solvent, and the temperature of pigmentation is in 50-
200℃。
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Cited By (2)
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| CN113278324A (en) * | 2021-06-01 | 2021-08-20 | 百合花集团股份有限公司 | Preparation method and application of modifying agent of azo organic pigment water-based ink |
| CN115772336A (en) * | 2022-11-15 | 2023-03-10 | 双乐颜料泰兴市有限公司 | Preparation of purple organic pigment |
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| CN113278324A (en) * | 2021-06-01 | 2021-08-20 | 百合花集团股份有限公司 | Preparation method and application of modifying agent of azo organic pigment water-based ink |
| CN113278324B (en) * | 2021-06-01 | 2022-04-01 | 百合花集团股份有限公司 | Preparation method and application of modifying agent of azo organic pigment water-based ink |
| CN115772336A (en) * | 2022-11-15 | 2023-03-10 | 双乐颜料泰兴市有限公司 | Preparation of purple organic pigment |
| CN115772336B (en) * | 2022-11-15 | 2024-02-20 | 双乐颜料泰兴市有限公司 | Preparation of purple organic pigment |
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